Dimethylformamide → 2-Methoxybenzoyl chloride

HRID 2055895Notes

Reaction equation

HRID 2055895 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:14])=O.CN(C)C=O>CCCCCC>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([Cl:14])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 113702-Methoxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 889692-Methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred solution of 2-Methoxy-benzoic Acid (6.5 g, 16 mmol) in hexane (60 mL) were added thionyl chloride (2.5 g, 21 mmol) and N,N-dimethylformamide (0.5 mL). The reaction mixture was heated to reflux for 1 h. After the reaction was complete, the solvent was evaporated under reduced pressure to yield the desired 2-Methoxy-benzoyl Chloride, which was redissolved in dichloromethane (50 mL) and used for the condensation with anilides.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a831892262a2457ea19a7f4c8828303c
Source dataset
uspto-grants-2008_02
Patent number
US07332629B2

Reaction notes

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